Patent GB-781702-A (GB)
Title: Herbicides and herbicidal compositions
IPC: C07D295/185
Filed: 1954-11-01
Abstract: The invention comprises N-substituted haloacetamides of the general formula: <FORM:0781702/IV (a)/1> wherein X represents a halogen atom, R1 represents hydrogen or an alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl group of not more than 6 carbon atoms, and R2 represents a heterocyclic group having one of the general formul : <FORM:0781702/IV (a)/2> (Y representing oxygen or sulphur and Z a hydrogen or halogen atom, or an alkyl group of up to 4 carbon atoms), and herbicidal compositions (see Group VI) containing them or containing compounds of the said general formula in which R1 has one of the stated meanings, R2 has one of the meanings stated for R1 (except hydrogen) or represents a cyclohexyl or benzyl group of the general formula: <FORM:0781702/IV (a)/3> or <FORM:0781702/IV (a)/4> or (when R1 is other than hydrogen) a group of the general formula: <FORM:0781702/IV (a)/5> or in which R1 and R2 together with the nitrogen atom form a 5- or 6-membered monocyclic heterocyclic ring which may contain oxygen or sulphur as an additional hetero atom and may contain one of the substituents denoted by Z.  The haloacetamides may be prepared by reacting the appropriate primary or secondary amine with a haloacetyl halide, preferably in the presence of aqueous sodium hydroxide below room temperature.  Examples describe the preparation of chloracetic acid diallylamide, cyclohexylamide, furfurylamide, b -chloroethylamide, di - n - propylamide, dipropargylamide, n-amylamide, b  - and g  - chloropropylamide, n-butylamide, di-n-butylamide, isoamylamide, diisoamylamide, g  - methoxypropylamide, b -and g  - chloroallylamide, di - (b  - chlorallyl)-amide, di - (b :g  - dichloropropyl) - amide, benzylamide, N - allylcyclohexylamide, tetrahydrofurfurylamide, thenylamide, 2 - p - thioxanylmethylamide, morpholide, piperidide, N-(b  - chloroallyl) - anilide, and N - methyl -, ethyl- and butyl-anilides, and bromoacetic acid diallylamide.  In a further example, the first three compounds are refluxed in acetone with potassium iodide to form the corresponding iodoacetamides. Reference is also made to fluoroacetamides.ALSO:Herbicidal compositions comprise, in admixture with a pulverulent solid or aqueous liquid dilutent, an N-substituted haloacetamide of the general formula <FORM:0781702/VI/1> wherein X represents a halogen and (a) R1 and R2 are selected from hydrogen atoms, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl groups of up to 6 carbon atoms, and alkoxyalkyl groups of up to 8 carbon atoms, not more than one being hydrogen, or (b) R1 is as defined under (a) and R2 is a cyclohexyl, benzyl or heterocyclic group having one of the general formulae <FORM:0781702/VI/2> , <FORM:0781702/VI/3> , <FORM:0781702/VI/4> , <FORM:0781702/VI/5> , <FORM:0781702/VI/6> , <FORM:0781702/VI/7> , <FORM:0781702/VI/8> , <FORM:0781702/VI/9> , <FORM:0781702/VI/100> , <FORM:0781702/VI/111> <FORM:0781702/VI/122> , (wherein Y is O or S and Z is hydrogen, halogen or an alkyl group of up to 4 carbon atoms), or (c) R1 is as defined under (a), excepting hydrogen, and R2 is a group of the general formula <FORM:0781702/VI/133> (where Z is as previously defined).  Particulars are given of the properties of chloracetic acid diallylamide, 2-chloroethylamide, benzylamide, cyclohexylamide, N - cyclohexyl - N - allylamide, 2 - furfurylamide, tetrahydrofurfurylamide, morpholide, piperidide, N-ethyl-p-chloranilide, N - ethylanilide, 3 - methoxypropylamide, isoamylamide, 2 : 3 - dichloropropylamide, 2 - chloroallylamide, N- methylanilide, N - cyclohexylanilide, di - n - propylamide and dipropargylamide, and bromo- and iodo-acetic acid diallylamides. Diluents specified are clays (e.g. china clays, bentonites and attapulgites), other minerals (e.g. talc, pyrophyllite, quartz, diatomaceous earth, fuller's earth, chalk, rock phosphate and sulphur), chemically modified materials (e.g. acid-washed bentonite, precipitated calcium phosphate, precipitated calcium carborate and colloidal silica), and water, if necessary with the addition of a dispensing agent (e.g. soaps, amine salts of long chain carboxylic acids, sulphonated animal, vegetable and mineral oils, quaternary salts of high molecular weight acids, rosin soaps, sulphuric acid salts of high molecular weight organic compounds, algin soaps, and ethylene oxide condensation products with fatty acids, alkyl phenols and mercaptans), and if desired in conjunction with organic solvents for the active components (e.g. isopropanol, benzene, acetone, methyl ethyl ketone, kerosene, and chlorinated hydrocarbons).